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Hotels in Middlesboro

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Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

2.5 out of 5
1260 N, 12th Street Middlesboro KY
  • 8 min walk from Middlesboro Mall
Book a stay at this business-friendly hotel in Middlesboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (819 reviews)
Belinda at the desk is amazing She made our stay excellent , she made us feel like we were old friends . We will be staying here on each visit .

Reviewed on Jan 24, 2026

Sleep Inn & Suites Middlesboro
Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG

2.5 out of 5
1252 N 12th St Middlesboro KY
  • 4 min walk from Middlesboro Mall
Book a stay at this business-friendly hotel in Middlesboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (701 reviews)
Clean room

Reviewed on Jan 14, 2026

Holiday Inn Express Middlesboro by IHG
Boone Trail Inn

Boone Trail Inn

2 out of 5
2105 US HIGHWAY 25 E Middlesboro KY
  • 18 min walk from Middlesboro Mall
Stay at this motel in Middlesboro. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
7.2/10 Good! (107 reviews)
The owners and staff were quite nice. The owner brought me a blanket without me having to ask since the temp was going to drop into the 40s. Inside,the owners have done an excellent update of the rooms.Excellent value for the money.

Reviewed on Oct 21, 2025

Boone Trail Inn
Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG

2.5 out of 5
56 West Highway 92 Williamsburg KY
  • 43 min drive from Middlesboro Mall
Stay at this hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9/10 Wonderful! (1,001 reviews)
Great staff, clean room and comfortable bed.

Reviewed on Jan 27, 2026

Holiday Inn Express Williamsburg by IHG
Pine Mountain State Resort Park

Pine Mountain State Resort Park

3 out of 5
1050 State Park Road Pineville KY
  • 22 min drive from Middlesboro Mall
Book a stay at this golf hotel in Pineville. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
9/10 Wonderful! (680 reviews)
Cabin was clean and well furnished

Reviewed on Jan 21, 2026

Pine Mountain State Resort Park
Super 8 by Wyndham Williamsburg

Super 8 by Wyndham Williamsburg

2.5 out of 5
30 W Highway 92 Williamsburg KY
  • 43 min drive from Middlesboro Mall
Stay at this hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
5.6/10 (784 reviews)
Everything was clean, but it really need some updates to make it more appealing! There was no tissues, the bathroom really needed renovated. It just needed freshened up. But it was nice and clean and staff seemed real nice

Reviewed on Jan 8, 2026

Super 8 by Wyndham Williamsburg
Days Inn by Wyndham Jellico - Tennessee State Line

Days Inn by Wyndham Jellico - Tennessee State Line

2 out of 5
1417 5th Street Jellico TN
  • 32 min drive from Middlesboro Mall
Book a stay at this spa hotel in Jellico. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.2/10 Good! (1,000 reviews)
It was clean

Reviewed on Jan 18, 2026

Days Inn by Wyndham Jellico - Tennessee State Line
The Olde Mill Inn Bed & Breakfast

The Olde Mill Inn Bed & Breakfast

2.5 out of 5
603 Pennlyn Avenue Cumberland Gap TN
  • 4 min drive from Middlesboro Mall
Stay at this B&B in Cumberland Gap. Enjoy free breakfast, free parking, and conference space. Our guests praise the breakfast in our reviews. Popular attractions ...
9.6/10 Exceptional! (179 reviews)
The staff was excellent. They are wonderful people. They made sure everything was perfect. We enjoyed having breakfast with the other guests. They addressed any allergy concerns and tailored your breakfast for all. I would recommend this bed and breakfast it is the best one we have ever stayed ...

Reviewed on Jan 18, 2026

The Olde Mill Inn Bed & Breakfast
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find cheap hotels in Middlesboro

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Choosing the right hotel in Kentucky has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Middlesboro’s 362 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $63. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Middlesboro hotel deals at the last minute.

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Frequently Asked Questions About Middlesboro hotels

Where can I find the best last-minute travel deals?

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How many hotels are there in Middlesboro?

With over 362 hotels in Middlesboro, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $63.

How to find cheap car rentals in Middlesboro?

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